Incremental Tuning Up of Fluorous Phenazine Acceptors

Castro, Karlee P.; Clikeman, Tyler T.; DeWeerd, Nicholas J.; Bukovsky, Eric V.; Rippy, Kerry C.; Kuvychko, Igor V.; Hou, Gao‐Lei; Chen, Yu‐Sheng; Wang, Xue‐Bin; Strauss, Steven H.; Boltalina, Olga V.

doi:10.1002/chem.201504122

Incremental Tuning Up of Fluorous Phenazine Acceptors

Journal Article · Mon Jan 11 23:00:00 EST 2016 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201504122· OSTI ID:1401639

Castro, Karlee P. ^[1]; Clikeman, Tyler T. ^[1]; DeWeerd, Nicholas J. ^[1]; Bukovsky, Eric V. ^[1]; Rippy, Kerry C. ^[1]; Kuvychko, Igor V. ^[1]; Hou, Gao‐Lei ^[2]; Chen, Yu‐Sheng ^[3]; Wang, Xue‐Bin ^[2]; Strauss, Steven H. ^[1]; Boltalina, Olga V. ^[1]

Department of Chemistry Colorado State University Fort Collins CO 80523 USA
Physical Sciences Division Pacific Northwest National Laboratory Richland WA 99352 USA
ChemMatCARS University of Chicago, Advanced Photon Source Argonne IL 60439 USA

Abstract

In a simple, one‐step direct trifluoromethylation of phenazine with CF ₃ I we prepared and characterized nine (poly)trifluoromethyl derivatives with up to six CF ₃ groups. The electrochemical reduction potentials and gas‐phase electron affinities show a direct, strict linear relation to the number of CF ₃ groups, with phenazine(CF ₃ ) ₆ reaching a record‐high electron affinity of 3.24 eV among perfluoroalkylated polyaromatics.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; AC02-06CH11357

OSTI ID:: 1401639

Alternate ID(s):: OSTI ID: 1242292
OSTI ID: 1254560

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 12 Vol. 22; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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